Perchloro-4-benzylidenecyclohexadienone | 144900-71-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Perchloro-4-benzylidenecyclohexadienone
• 英文别名: 2,3,5,6-tetrachloro-4-[chloro-(2,3,4,5,6-pentachlorophenyl)methylidene]cyclohexa-2,5-dien-1-one
• CAS: 144900-71-0
• 化学式: C₁₃Cl₁₀O
• 分子量: 526.672
• InChiKey: PBIUUFLAVFFNOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.86
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  perchlorodiphenylmethyl radical 在 氧气 作用下， 以 四氯化碳 为溶剂， 反应 2.0h， 以30%的产率得到六氯苯
  参考文献：
  名称：

  Photochemical behavior of stable free radicals: the photochemistry of perchlorodiphenylmethyl radical

  摘要：

  The excitation of perchlorodiphenylmethyl radical (PDM) at 530 nm leads to the lowest excited doublet, D1 (tau = 31 ns), from which emission is observed (PHI = 1 X 10(-3) +/- 0.0003). This state is quenched by electron donors and acceptors at a rate at or close to diffusion control and at much slower rates by oxygen and hydrogen atom donors. Fragmentation of PDM (PHI(d) = 0.06) occurs from a higher excited doublet (D(n), n greater-than-or-equal-to 2) producing intermediates that are trapped by O2, chlorine, or hydrogen donors, yielding products 1-6. Experimental evidence suggests a structure-photoreactivity correlation in the perchlorinated arylmethyl radicals in which the partitioning between photochemical cyclization or fragmentation depends on the twist angle between the appended phenyl rings.

  DOI：

  10.1021/j100103a025